Azobisisobutyronitrile → 6-(Bromomethyl)-2-methylquinoline

HRID 1173976

Reaction equation

HRID 1173976 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[N:3]=1.[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 134142,6-DimethylquinolineHCID 67184N-bromobutanimide

Product 1

HCID 27954806-(Bromomethyl)-2-methylquinolineYield 27.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In carbon tetrachloride (26 ml), 2,6-dimethylquinoline (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (1.0398 g), N-bromosuccinimide (1.2353 g), and azobisisobutyronitrile (98.5 mg) were dissolved and then the whole was subjected to thermal reflux for 2 hours under an argon atmosphere. After the reaction, a precipitate was removed through filtration and then washed with water, followed by drying with magnesium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (427.3 mg) as a white solid.

Workup

  1. temperaturethermal reflux for 2 hours under an argon atmosphere
  2. customAfter the reaction
  3. customa precipitate was removed through filtration
  4. washwashed with water
  5. dry with materialby drying with magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-621068ad687841ff8c58d580112f94c8
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Linked notes

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